Shelter Island Vacations from ₩1,205,254
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The Latest Shelter Island Vacation Packages
Price found within the past 48 hours. Click for updated prices.
OYO Times Square
Manhattan
Save 100% on your flight
Price was ₩1,885,122, price is now ₩1,205,254 per person
₩1,205,254
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,773 reviews)
Great locations. That is the dirtiest room I have stayed in in quite some time. The location was great and the room was adequate for a night.
Reviewed on Mar 14, 2026
Hotel Riu Plaza Manhattan Times Square
Manhattan
Save 100% on your flight
Price was ₩3,187,499, price is now ₩1,791,882 per person
₩1,791,882
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,450 reviews)
The location is perfect—close to everything, which made getting around really easy. The hotel was very clean and well maintained. Breakfast was excellent with plenty of options, and everything was very well organized even when it was busy. Overall, a very comfortable and convenient place to stay. I would definitely recommend it.
Reviewed on Mar 15, 2026
Hotel Riu Plaza New York Times Square
Manhattan
Save 100% on your flight
Price was ₩3,012,676, price is now ₩1,707,036 per person
₩1,707,036
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,923 reviews)
Great location. Great service. Great value. Regular beds were great. Pull out coach was fair. We were three men staying here. The only thing poor was the buffet breakfast. If you like all you can eat buffets then it was fine however quality of food was fair and coffee options were fair. We ended up eating at local diners because they were more intimate and the food quality was much better. Overall, I would stay here again.
Reviewed on Mar 14, 2026
Hotel St. James
Manhattan
Save 100% on your flight
Price was ₩2,412,737, price is now ₩1,434,818 per person
₩1,434,818
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (7,024 reviews)
It was really good overall!!
Reviewed on Mar 16, 2026
Hard Rock Hotel New York
Manhattan
Save 100% on your flight
Price was ₩2,429,930, price is now ₩1,680,324 per person
₩1,680,324
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Seattle (SEA) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (5,389 reviews)
This hotel really was a beautiful building. It smelt really nice and the decor was stunning. We stayed in a deluxe king room which was nice because it had a beautiful bathtub. Unfortunately i was only able to take one bath because the plug was broken and got stuck the first night and they ended up just taking the entire plug out so i couldnt take another bath. This hotel also allows you to keep bags with the bellhop so you dont have to carry them around the city on the days you arrive and leave. As far as location goes it is in a very conventient spot but as far as views from the room or rooftop bar goes... you really cannot see times square from either.
Reviewed on Mar 16, 2026
Where to stay in Shelter Island
Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
290 Old Montauk Highway Montauk NY
The price is ₩573,104 per night from Mar 17 to Mar 18
₩573,104
₩785,724 total
Mar 17 - Mar 18
includes taxes & fees
8.4/10 Very Good! (738 reviews)
I took my husband for a relaxing weekend for his birthday at Gurneys Resort. We had an ocean front room with a beautiful view! The room and resort was beautiful and clean. We hung out at GiGis bar a lot and the bar tenders were great! Super friendly and helpful! I loved our stay however I was truly ...
Reviewed on Mar 4, 2026
Montauk Manor
236 Edgemere St. Montauk NY
The price is ₩173,055 per night from Mar 17 to Mar 18
₩173,055
₩227,039 total
Mar 17 - Mar 18
includes taxes & fees
9.2/10 Wonderful! (1,304 reviews)
Amazing!
Reviewed on Mar 15, 2026
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ₩200,923 per night from Apr 1 to Apr 2
₩200,923
₩256,915 total
Apr 1 - Apr 2
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Excellent place to stay, water view
Reviewed on Mar 12, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
